Direct-Booking Hotel Upgrade Method
- Difficulty
- Starter
- Time to result
- ~days to results
- Steps
- 4
- Confidence
- —
Chris uses a simple relationship-building sequence to improve hotel stays without directly demanding perks. He generally books with the hotel rather than through an intermediary, obtains an email address for the general manager or another appropriate contact, and sends a short message expressing genuine excitement about the stay. If the visit marks a real celebration, he mentions it, but he does not fabricate an occasion. Three days before arrival, he follows up to confirm that the trip is still happening. Chris reports that this approach has frequently resulted in upgrades, breakfast, champagne, or other amenities. The mechanism is hospitality: direct guests give the hotel an opportunity to build a continuing customer relationship.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Book directly
Reserve the stay through the hotel when the direct terms remain competitive.
Pro tip Compare the direct rate with unusually large private or promotional discounts before deciding.
Watch out Chris does not insist on direct booking when another channel offers a substantially better deal.
- 2
Find a hotel contact
Locate a general manager or suitable hotel contact, calling the front desk for an email address if necessary.
Pro tip Use a role-based contact if a named manager is unavailable.
- 3
Send an enthusiasm email
State that the reservation has been made, identify the traveling party, and express genuine excitement about the stay.
Pro tip Mention a celebration only when one is actually occurring.
Watch out Do not falsely claim that every trip is a honeymoon or special occasion.
- 4
Confirm three days before arrival
Follow up shortly before check-in to confirm that the visit is proceeding and reiterate enthusiasm.
Pro tip Keep the message short and avoid asking directly for an upgrade.
Watch out Perks are discretionary and not guaranteed.
In the wild
Using the direct-booking and email sequence, Chris says he has seen an approximately 50% hit rate for some form of extra hospitality. Outcomes have included room upgrades, free breakfast, champagne, chocolate-covered strawberries, and once even initials embroidered on a pillow.
→ A brief, genuine contact sometimes improved the stay at no stated additional cost.
Common mistakes
Fabricating a celebration
Chris explicitly rejects falsely telling every hotel that the trip is a honeymoon.
Demanding a perk
His message expresses excitement and lets the hotel choose whether to offer anything.
Ignoring a much better rate
Direct booking can help build a relationship, but Chris will use another option when the discount is sufficiently large.
From the transcript
“book a hotel book directly with the hotel don't use booking.com don't use Trip Advisor book directly with the hotel”
“three days before checkin follow up and say hey just want to let you know we're still coming”
“I have seen almost let's say 50% hit rate on getting upgrade free breakfast bottle of champagne you know chocolate covered strawberries one time initials…”
From the episode
Simple Hacks To Optimise Your Life - Chris Hutchins (All The Hacks Podcast)